(2R)-heptadec-12-en-2-ol

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: (2R)-heptadec-12-en-2-ol
• 化学式: C₁₇H₃₄O
• 分子量: 254.5
• InChiKey: ITCDZRKXSLKGSB-QGZVFWFLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.8
• 重原子数：
  18
• 可旋转键数：
  13
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

文献信息

• Method for Producing (Z)-2-Benzoyloxy-12-Heptadecene and (2S,12Z)-2-Hydroxy-12-Heptadecene and Method for Producing (2S,12Z)-2-Acetoxy-12-Heptadecene
  申请人：Shin-Etsu Chemical Co., Ltd.

  公开号：US20160076063A1

  公开（公告）日：2016-03-17

  Provided are methods including a method for industrially producing (2S,12Z)-2-acetoxy-12-heptadecene, which is, for example, a sex pheromone of pistachio twig borer. The methods can include a production method comprising a step of reacting racemic (2RS,12Z)-2-hydroxy-12-heptadecene with vinyl benzoate in the presence of a lipase to obtain a mixture of optically active (2R,12Z)-2-benzoyloxy-12-heptadecene of Formula (R,Z-2) and optically active (2S,12Z)-2-hydroxy-12-heptadecene of Formula (S,Z-1), a step of heating the mixture to distill out the optically active (2S,12Z)-2-hydroxy-12-heptadecene (S,Z-1), and a step of acetylating the optically active (2S,12Z)-2-hydroxy-12-heptadecene (S,Z-1) to obtain optically active (2S,12Z)-2-acetoxy-12-heptadecene of Formula (S,Z-3).

  提供的方法包括一种用于工业生产(2S,12Z)-2-乙酰氧基-12-庚烯的方法，例如，这是开心果枝小蠹的性信息素。该方法可以包括一个生产方法，其中包括以下步骤：在脂肪酶存在下，将外消旋(2RS,12Z)-2-羟基-12-庚烯与苯乙烯酸乙酯反应，以获得光学活性的(2R,12Z)-2-苯甲酰氧基-12-庚烯混合物（式（R,Z-2））和光学活性的(2S,12Z)-2-羟基-12-庚烯（式（S,Z-1）），加热混合物以蒸馏出光学活性的(2S,12Z)-2-羟基-12-庚烯（S,Z-1），乙酰化光学活性的(2S,12Z)-2-羟基-12-庚烯（S,Z-1）以获得光学活性的(2S,12Z)-2-乙酰氧基-12-庚烯（式（S,Z-3））。
• METHOD FOR PRODUCING (Z)-2-BENZOYLOXY-12-HEPTADECENE AND (2S,12Z)-2- HYDROXY-12-HEPTADECENE AND METHOD FOR PRODUCING (2S,12Z)-2-ACETOXY-12- HEPTADECENE
  申请人：Shin-Etsu Chemical Co., Ltd.

  公开号：EP2998286A1

  公开（公告）日：2016-03-23

  Provided are methods including a method for industrially producing (2S,12Z)-2-acetoxy-12-heptadecene, which is, for example, a sex pheromone of pistachio twig borer. The methods can include a production method comprising a step of reacting racemic (2RS,12Z)-2-hydroxy-12-heptadecene with vinyl benzoate in the presence of a lipase to obtain a mixture of optically active (2R,12Z)-2-benzoyloxy-12-heptadecene of Formula (R,Z-2) and optically active (2S,12Z)-2-hydroxy-12-heptadecene of Formula (S,Z-1), a step of heating the mixture to distill out the optically active (2S,12Z)-2-hydroxy-12-heptadecene (S,Z-1), and a step of acetylating the optically active (2S,12Z)-2-hydroxy-12-heptadecene (S,Z-1) to obtain optically active (2S,12Z)-2-acetoxy-12-heptadecene of Formula (S,Z-3).

  本发明提供的方法包括一种工业化生产(2S,12Z)-2-乙酰氧基-12-十七烯的方法，例如，它是开心果树枝蛀虫的一种性信息素。这些方法可以包括一种生产方法，该方法包括以下步骤：在脂肪酶存在下，将外消旋(2RS,12Z)-2-羟基-12-十七烯与苯甲酸乙烯酯反应，得到光学活性的式(R,Z-2)(2R,12Z)-2-苯甲酰氧基-12-十七烯和光学活性的式(R,Z-2)(2S,12Z)-2-羟基-12-十七烯的混合物、12Z)-2-羟基-12-十七烯的混合物，加热该混合物以蒸馏出光学活性(2S,12Z)-2-羟基-12-十七烯(S,Z-1)的步骤，以及乙酰化光学活性(2S,12Z)-2-羟基-12-十七烯(S,Z-1)以获得光学活性(2S,12Z)-2-乙酰氧基-12-十七烯的式(S,Z-3)的步骤。
• Method for producing (Z)-2-benzoyloxy-12-heptadecene and (2S,12Z)-2-hydroxy-12-heptadecene and method for producing (2S,12Z)-2-acetoxy-12-heptadecene
  申请人：Shin-Etsu Chemical Co., Ltd.

  公开号：US10081820B2

  公开（公告）日：2018-09-25

  Provided are methods including a method for industrially producing (2S,12Z)-2-acetoxy-12-heptadecene, which is, for example, a sex pheromone of pistachio twig borer. The methods can include a production method comprising a step of reacting racemic (2RS,12Z)-2-hydroxy-12-heptadecene with vinyl benzoate in the presence of a lipase to obtain a mixture of optically active (2R,12Z)-2-benzoyloxy-12-heptadecene of Formula (R,Z-2) and optically active (2S,12Z)-2-hydroxy-12-heptadecene of Formula (S,Z-1), a step of heating the mixture to distill out the optically active (2S,12Z)-2-hydroxy-12-heptadecene (S,Z-1), and a step of acetylating the optically active (2S,12Z)-2-hydroxy-12-heptadecene (S,Z-1) to obtain optically active (2S,12Z)-2-acetoxy-12-heptadecene of Formula (S,Z-3).

  本发明提供的方法包括一种工业化生产(2S,12Z)-2-乙酰氧基-12-十七烯的方法，例如，它是开心果树枝蛀虫的一种性信息素。这些方法可以包括一种生产方法，该方法包括以下步骤：在脂肪酶存在下，将外消旋(2RS,12Z)-2-羟基-12-十七烯与苯甲酸乙烯酯反应，得到光学活性的式(R,Z-2)(2R,12Z)-2-苯甲酰氧基-12-十七烯和光学活性的式(R,Z-2)(2S,12Z)-2-羟基-12-十七烯的混合物、12Z)-2-羟基-12-十七烯的混合物，加热该混合物以蒸馏出光学活性(2S,12Z)-2-羟基-12-十七烯(S,Z-1)的步骤，以及乙酰化光学活性(2S,12Z)-2-羟基-12-十七烯(S,Z-1)以获得光学活性(2S,12Z)-2-乙酰氧基-12-十七烯的式(S,Z-3)的步骤。
• METHOD FOR PRODUCING (Z)-2-BENZOYLOXY-12-HEPTADECENE AND (2S,12Z)-2-HYDROXY-12-HEPTADECENE AND METHOD FOR PRODUCING (2S,12Z)-2-ACETOXY-12-HEPTADECENE
  申请人：Shin-Etsu Chemical Co., Ltd.

  公开号：US20180355386A1

  公开（公告）日：2018-12-13

  Provided are methods including a method for industrially producing (2S,12Z)-2-acetoxy-12-heptadecene, which is, for example, a sex pheromone of pistachio twig borer. The methods can include a production method comprising a step of reacting racemic (2RS,12Z)-2-hydroxy-12-heptadecene with vinyl benzoate in the presence of a lipase to obtain a mixture of optically active (2R,12Z)-2-benzoyloxy-12-heptadecene of Formula (R,Z-2) and optically active (2S,12Z)-2-hydroxy-12-heptadecene of Formula (S,Z-1), a step of heating the mixture to distill out the optically active (2S,12Z)-2-hydroxy-12-heptadecene (S,Z-1), and a step of acetylating the optically active (2S,12Z)-2-hydroxy-12-heptadecene (S,Z-1) to obtain optically active (2S,12Z)-2-acetoxy-12-heptadecene of Formula (S,Z-3).
• [EN] COMPOSITION OF CHEMICALS FOR MANIPULATING THE BEHAVIOUR OF THE PISTACHIO TWIG BORER, KERMANIA PISTACIELLA (LEPIDOPTERA: OINOPHILIDAE)<br/>[FR] COMPOSITION DE SUBSTANCES CHIMIQUES POUR LA MANIPULATION DU COMPORTEMENT DE LA PETITE MINEUSE DU PISTACHIER, KERMANIA PISTACIELLA (LEPIDOPTERA : OINOPHILIDAE)
  申请人：GRIES REGINE

  公开号：WO2007079563A1

  公开（公告）日：2007-07-19

  [EN] The invention relates to a composition and procedure for manipulating the behavior of the pistachio twig borer, K. pistaciella. More specifically, this innovation relates to the preparation and use of (12Z)-2-acetoxy-12-heptadecene, or enantiomers thereof, and of (12Z)-2-hydroxy-heptadecene, or enantiomers thereof, for manipulating the behavior of K. pistaciella.
  [FR] La présente invention concerne une composition et un mode opératoire destinés à la manipulation du comportement de la petite mineuse du pistachier, K. pistaciella. Plus spécifiquement, la présente invention concerne la synthèse et l'utilisation de (12Z)-2-acétoxy-12-heptadécène, ou de ses énantiomères, et de (12Z)-2-hydroxy-heptadécène, ou de ses énantiomères, pour la manipulation du comportement de K. pistaciella.